Regiospecific Synthesis of Tetra-Substituted Furans

Leiv K. Sydnes; Rustem Isanov; Myagmarsuren  Sengee; Francesco Livi

doi:10.1080/00397911.2012.748076

Regiospecific Synthesis of Tetra-Substituted Furans

Leiv K. Sydnes, Rustem Isanov, Myagmarsuren Sengee, Francesco Livi

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Abstract

α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.

Original language	English
Journal	Synthetic Communications
Volume	43
Issue number	21
Pages (from-to)	2898-2905
ISSN	0039-7911
DOIs	https://doi.org/10.1080/00397911.2012.748076
Publication status	Published - 2013
Externally published	Yes

Bibliographical note

Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.

Keywords

Conjugated acetylenic ketones
Ketoesters
Propargylic alcohols

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title = "Regiospecific Synthesis of Tetra-Substituted Furans",

abstract = "α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.",

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T1 - Regiospecific Synthesis of Tetra-Substituted Furans

AU - Sydnes, Leiv K.

AU - Isanov, Rustem

AU - Sengee, Myagmarsuren

AU - Livi, Francesco

N1 - Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.

PY - 2013

Y1 - 2013

N2 - α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.

AB - α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.

KW - Conjugated acetylenic ketones

KW - Ketoesters

KW - Propargylic alcohols

U2 - 10.1080/00397911.2012.748076

DO - 10.1080/00397911.2012.748076

M3 - Journal article

VL - 43

SP - 2898

EP - 2905

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 21

ER -